Fungal polyketides from a rhizospheric soil-derived Penicillium sp. YUD17004 associated with Gastrodia elata

Hong-Tao Li; Rui-Ning Yang; Tao Liu; Fei Xie; Hao-Jie Duan; Dan-Dan Xia; Hao Zhou; Zhong-Tao Ding

doi:10.1016/j.phytochem.2022.113475

Fungal polyketides from a rhizospheric soil-derived Penicillium sp. YUD17004 associated with Gastrodia elata

Phytochemistry. 2023 Jan:205:113475. doi: 10.1016/j.phytochem.2022.113475. Epub 2022 Oct 18.

Authors

Hong-Tao Li¹, Rui-Ning Yang², Tao Liu², Fei Xie², Hao-Jie Duan², Dan-Dan Xia², Hao Zhou³, Zhong-Tao Ding⁴

Affiliations

¹ School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, 650500, China.
² Key Laboratory of Functional Molecules Analysis and Biotransformation of Universities in Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China.
³ Key Laboratory of Functional Molecules Analysis and Biotransformation of Universities in Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China. Electronic address: haozhou@ynu.edu.cn.
⁴ Key Laboratory of Functional Molecules Analysis and Biotransformation of Universities in Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China; College of Pharmacy, Dali University, Dali, 671000, China. Electronic address: ztding@ynu.edu.cn.

PMID: 36270411
DOI: 10.1016/j.phytochem.2022.113475

Abstract

Five unprecedented polyketide metabolites were isolated and characterized from a rhizospheric soil-derived Penicillium sp. YUD17004. Their diverse structures included two indanone-type polyketides penicillyketides A and B, a phthalide-like polyketides penicillyketide C, a symmetrical chromone dimer penicillyketide D, along with a pyrone derivative pyranlyketide, which were elucidated by spectroscopic data interpretation and quantum chemical electronic circular dichroism calculation. Notably, the structures of penicillyketides A and B feature a highly functionalized indanone ring nucleus, but differ from other indanone-containing polyketides by the alkyl substitution pattern. The structure of penicillyketide C comprises a furanone ring instead of the hydroxycyclopentenone ring characteristic for penicillyketides A and B, and represents an undescribed arrangement within C₁₇ polyketides. Penicillyketide D represented the first example of a chromone homodimer with the bridge at C-2/2'. Penicillyketide B exhibited weak anti-inflammatory activity with an IC₅₀ value of 32 ± 1.0 μM. Penicillyketide D displayed weak cytotoxicity against MCF-7 cell line with an IC₅₀ value of 25 ± 0.9 μM.

Keywords: Anti-inflammatory activity; Chromone dimer; Cytotoxicity; Fungal polyketides; Indanone; Penicillium sp.; Phthalide; Trichocomaceae.

MeSH terms

Gastrodia*
Penicillium*
Polyketides* / pharmacology
Soil

Substances

Polyketides
Soil